It is known that a variety of fimbrolides possessing antifungal and antimicrobial properties can be isolated from red marine algae Delisea fimbriata, Delisea elegans and Delisea pulchra. The very few reported syntheses of functionalised fimbrolides use (E)-β-bromo-β-lithioacrylate or 3-formyl-6-methylfuran or allenes as starting materials. These syntheses are unnecessarily long, tedious and give very low yields of the fimbrolides. The present inventors have recently reported the preparation of a range of fimbrolides having different sized chain lengths (Manny et al (1997) Tetrahedron 53: 15813–15826, the disclosure of which is incorporated herein by reference).
Prior to the present invention, it had not been appreciated that the side chains of the fimbrolides could be functionalised directly affording a variety of halogen or oxygen functionalised fimbrolides. We have found that fimbrolides behave like allylic or benzylic compounds in their reactivity and consequently are amenable to free radical functionalisation. The derived halogen compounds can be converted to alcohols or to esters directly from the halogen derivatives or to ketones, esters, amides, alcohols or other halides indirectly from the corresponding esters or alcohols. The fimbrolides substituted with an appropriate group in the alkyl chain are capable of yielding polymers through that group, either directly or via copolymerisation with suitable monomers. It is the preparation of these fimbrolide-based halides, alcohols, esters, ethers, amines, amides, and nitro compounds, ketones, oligomers and polymers that form the major aspect of this invention.
The fimbrolides prepared in accordance with the present invention include not only synthetic versions of the two naturally occurring fimbrolides, but also other functionalised fimbrolides which we believe to be novel compounds. The compounds synthesised in accordance with the present invention may be according to formula (I):

wherein R6 is H, OH, alkyl, alkoxy, oxoalkyl, alkenyl, aryl or arylalkyl whether unsubstituted or substituted, straight chain or branched chain, hydrophobic, hydrophilic or fluorophilic;
R2 and R3 are independently or both H or halogen;
R9 is halogen;
Z is independently selected from the group R6, halogen, OOH, OC(O)R6, ═O, amine, azide, thiol, R6, mercaptoalkyl, alkenyloxy, mercaptoalkenyl, aryloxy, mercaptoaryl, arylalkyloxy, mercaptoarylalkyl, SC(O)R6, OS(O)R6, OS(O)2R6, NHC(O)R6═NR4 or NHR4; and                R4 is OH, alkyl, alkoxy, poly(ethylene glycol), alkenyl, aryl or arylalkyl.        
Compounds according to Formula (I), apart from those in which R1=propyl, R2=Br, R3=H, R9=Br and Z is OC(O)CH3 or OH, are believed to be novel and form part of the present invention.
In the structural formulae given herein, a particular geometry is not to be taken as specified unless specifically stated. For example, the formulae are intended to cover the both Z-isomers and E-isomers.